N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoroadenosine
[CAS# 136834-21-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoroadenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-fluoro-4-hydroxyoxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₃₈H₃₄FN₅O₆
• Molecular Weight: 675.70
• CAS Registry Number: 136834-21-4
• SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7)F)O

Properties

• Solubility: Insoluble (6.7E^-7 g/L) (25 ºC), Calc.^*
• Density: 1.35±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoroadenosine is a synthetic nucleoside analog designed to enhance stability, cellular uptake, and biological activity. The compound features multiple protecting groups and modifications that improve its utility in therapeutic and research applications.

The development of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoroadenosine represents an innovative step forward in nucleoside chemistry. The researchers aimed to create a compound that would resist enzymatic degradation and have improved pharmacokinetic properties. By adding a benzoyl group to the N-position of the deoxyribose sugar, a bis(4-methoxyphenyl)benzyl (DMT) group to the 5' position, and a fluorine atom to the 2' position, the scientists enhanced the stability and functionality of this nucleoside.

This nucleoside analog has several key structural modifications: the N-benzoyl group enhances chemical stability and lipophilicity, improving cellular uptake; the DMT group protects the 5' hydroxyl group, facilitating oligonucleotide synthesis; and the 2'-deoxy-2'-fluoro substitution enhances resistance to enzymatic degradation and enhances stability in biological environments.

The protecting groups on N-benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoroadenosine prevent degradation and unwanted side reactions during biochemical processes. The DMT group ensures selective deprotection during oligonucleotide synthesis, while the 2'-fluoro substitution provides stability by resisting nuclease activity. The benzoyl group enhances cellular uptake, ensuring efficient delivery and incorporation into DNA or RNA.

This nucleoside analog shows promise in antiviral therapy. Its stability and ability to integrate into viral DNA make it a candidate for inhibiting viral replication, potentially treating infections such as HIV and hepatitis.

N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoroadenosine has been studied for its anticancer properties. By incorporating into the DNA of rapidly dividing cancer cells, it can disrupt replication and induce cell death, making it a potential chemotherapeutic agent.

This compound is essential for the synthesis of oligonucleotides for research and therapeutic applications. Its protecting groups ensure accurate and efficient assembly of DNA and RNA sequences, thereby promoting advances in genetic research and therapy.

In research, this modified nucleoside facilitates the study of nucleic acid interactions and the effects of nucleoside modifications on DNA and RNA stability and function. Its enhanced stability allows researchers to study these processes more efficiently.

The fluorine substitution and protecting groups significantly increase resistance to enzymatic degradation, and the N-benzoyl group enhances cellular uptake and stability. This compound can be used in antiviral, anticancer, and molecular biology research. However, the synthesis of this modified nucleoside can be very complex and costly, and further research is needed to optimize its therapeutic effects and minimize potential side effects.